The night I landed in Bermuda, I almost turned around.
Not because of the flight.
But because of what waited on the other end of it: gale-force rain blowing sideways across the tarmac, and an Immigration Officer who stopped me because I didn’t have a return flight booked. I was held in Immigrations and drilled for details on why I was on the island and who I was planning to meet with and who I was working for.
I remember sitting in the immigration office, soaked, holding a one-way ticket, wondering if I’d made a mistake I couldn’t undo. I had left the comfort of my family and my daughter had just started her senior year of high school. Had I made a mistake?
I’d like to tell you I felt brave that night. I didn’t. I felt like someone who’d just left everything that made sense, standing in a fluorescent-lit room on an island I’d never set foot on, being asked to prove I had a reason to be there.
I said a prayer — the kind you say when you don’t have a Plan B, and only a plan for moving forward.
After letting the Gate Agent take my credit card and passport to book a return flight, they let me through. My driver was the last one standing in the reception terminal. He led me out into the storm and safely delivered me to my hotel, and that was that.
Day one.
Morning changes everything
I woke up to a version of Bermuda the storm hadn’t let me see the night before.
Water that didn’t look like any water I’d seen before. It was a particular shade of turquoise that photographs never quite get right, and I won’t try to describe it better than that either.
Pastel houses stepping down toward the harbor.
And people — strangers — looking me in the eye on the sidewalk and saying good morning like they meant it.
That’s not a small thing. Most places I’d lived, you could walk six blocks and make eye contact with exactly no one. In Bermuda, not saying hello back would have been the strange choice. It took me a few days to stop being surprised by it, and longer than that to understand why it mattered so much.
Falling in love slowly
I didn’t fall for Bermuda in a week, or a month. It happened the way most real things happen, slowly. And then you look up and realize the people and island have already stolen your heart.
Some of it was the traditions the island holds onto on purpose.
Churches that still fill on Sunday.
A pace of life that refuses to apologize for itself, even as the rest of the world speeds up around it. I’ll tell you more about that.
Some of it was family, not just mine, but the way Bermuda treats family as the whole architecture of a life.
It’s a small island.
Everyone is connected to everyone, a few generations deep, and that connection isn’t incidental. It is protected, on purpose, the way you’d protect anything you couldn’t replace.
And some of it was pride — the quiet, working kind.
Bermuda is a rock in the middle of the Atlantic with almost nothing in the way of natural resources, and the people who live there have built real lives on it anyway, generation after generation.
There’s a man who stood on a roundabout every single morning for decades, waving at every car that passed, and the whole island waved back. That’s its own story. I’m not going to rush it here.
Getting started…my stories
This is the first post in a series about the island that changed how I understood travel — long before Standfast Travel existed.
Over the next several weeks, I’ll walk through the traditions, the pride, the food, the history, and the places that made me love it the way I do.
If you’ve ever landed somewhere as a stranger and left as something closer, you already know where this is going.
If Bermuda has been on your list — or if it’s never occurred to you— I’d love to talk about what a trip there could look like for you.
Let’s talk….we’re listening!
We’d love to plan your Bermuda vacation so you can experience the island and fall in love, just like we did.
